Cross-dressing has been a staple of American Hollywood comedies since the days of silent comics like Roscoe “Fatty” Arbuckle, but the late Tony Curtis – who passed away in his sleep last night at age 85 – gave what remains perhaps the most memorable turn of a man donning feminine attire in Billy Wilder’s much-cherished 1959 comedy Some Like It Hot.

Born Bernard Schwartz on June 3rd, 1925 in New York, Curtis developed a love for the film industry at a very young age.  He was injured overseas while serving during World War II, after which he returned to New York and began to pursue a career in acting.  He eventually landed a seven-year contract with Universal Studios in 1948.

Curtis began to gain critical notice following his turn as the press agent Sidney Falco in the 1957 classic Sweet Smell of Success.  He received his sole Oscar-nomination the next year for his performance as John “Joker” Jackson, a white racist who escapes from prison while handcuffed to a black man named Noah Cullen (Sidney Poitier) in Stanley Kramer’s The Defiant Ones.

His next role was that of Joe, a jazz musician who – along with his companion, Jerry (Jack Lemmon) – must go into hiding after the two witness the infamous Saint Valentine’s Day massacre of 1929 in Wilder’s Some Like It Hot.  The two characters decide to don women’s clothing and join an all-ladies band, whose numbers include that of the beautiful but flighty singer Sugar Kane Kowalczyk (Marilyn Monroe) – needless to say, memorable hijinks ensue.

L to R: Curtis, Lemmon, and Monroe in ‘Some Like it Hot.’

The 1960s were a difficult time for Curtis, who struggled with drugs and alcohol addiction before he began a career on television shows like Michael Mann’s Vegas and the Roger Moore-starring series The Persuaders! during the 1970s.

Curtis eventually overcame his addiction issues during the 1980s and became renowned as a painter with a talent for crafting Matisse-like still lifes.  He also settled into a career as a writer and penned two works about his life – Tony Curtis: The Autobiography in 1993 and American Prince: A Memoir in 2008.

Curtis was an enormous talent whose artistic abilities reached far beyond that of the big screen.  He is survived by his wife, Jill Vandenberg Curtis, and seven children, including actress Jamie Lee Curtis.  We offer our condolences to his friends and family in this time of grief.

R.I.P. Tony Curtis (June 3rd, 1925-September 29th, 2010)